WO2013055524A1 - Liquid stabilizer mixtures - Google Patents

Liquid stabilizer mixtures Download PDF

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Publication number
WO2013055524A1
WO2013055524A1 PCT/US2012/057501 US2012057501W WO2013055524A1 WO 2013055524 A1 WO2013055524 A1 WO 2013055524A1 US 2012057501 W US2012057501 W US 2012057501W WO 2013055524 A1 WO2013055524 A1 WO 2013055524A1
Authority
WO
WIPO (PCT)
Prior art keywords
parts
weight
temperature
tert
liquid blend
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2012/057501
Other languages
English (en)
French (fr)
Inventor
Jiong YU
Roswell Easton King
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP12840357.3A priority Critical patent/EP2766419B1/en
Priority to KR1020147009357A priority patent/KR102013969B1/ko
Priority to SG11201401069TA priority patent/SG11201401069TA/en
Priority to CN201280049692.8A priority patent/CN104114628B/zh
Priority to RU2014118603/04A priority patent/RU2600321C2/ru
Priority to IN2605CHN2014 priority patent/IN2014CN02605A/en
Priority to BR112014008472A priority patent/BR112014008472A2/pt
Priority to CA2850191A priority patent/CA2850191C/en
Priority to JP2014535734A priority patent/JP6045001B2/ja
Priority to US14/345,998 priority patent/US9045618B2/en
Publication of WO2013055524A1 publication Critical patent/WO2013055524A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
    • C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only

Definitions

  • the present invention relates to processes for providing stable liquid blends of a) pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate,
  • liquid blends of stabilizers are useful as stabilizers for organic materials, for instance synthetic polymer stabilization.
  • tris-(2,4-di-tert-butylphenyl)phosphite are well known polymer stabilizers, commercially available as IRGANOX 1010, IRGANOX 1076 and IRGAFOS 168 respectively.
  • IRGANOX 1010 and IRGANOX 1076 are hindered phenolic antioxidants and IRGAFOS 168 is a phosphite processing stabilizer.
  • IRGANOX 1010 is:
  • IRGANOX 1076 is:
  • IRGAFOS 168 Tris-(2,4-di-tert-butylphenyl)phosphite, IRGAFOS 168 is:
  • IRGANOX 1010 has a melting point of ca. 120°C.
  • IRGANOX 1076 has a melting point of ca. 56°C.
  • IRGAFOS 168 melts at ca. 185°C.
  • a liquid blend could be pumped to be incorporated into a polymer during melt processing or during solution polymerization. Dosing would be more accurate and incorporation would be easier to perform.
  • c) tris-(2,4-di-tert-butylphenyl)phosphite which process comprises preparing a solid mixture comprising about 2 parts to about 3 parts by weight a), about 2 parts to about 3 parts by weight b) and about 2 parts to about 12 parts by weight c), heating the mixture to 185°C or higher for a sufficient time to obtain a clear liquid blend of a), b) and c), cooling the liquid blend to a temperature of from 90°C to 140°C and maintaining the liquid blend at a temperature of from 90°C to 140°C, where the liquid blend of a), b) and c) is stable at the temperature at which it is maintained for greater than 120 hours.
  • the process comprises preparing a solid mixture comprising about 5 parts to about 1 1 parts by weight c).
  • the process comprises preparing a solid mixture comprising about 8 parts to about 1 1 parts by weight c).
  • the liquid blend of a), b) and c) is maintained at a temperature of from 90°C to 125°C.
  • the liquid blend of a), b) and c) is maintained at a temperature of from 90°C to 1 10°C.
  • octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and c) tris-(2,4-di-tert-butylphenyl)phosphite which process comprises preparing a solid mixture comprising about 2 parts to about 3 parts by weight a) and about 2 parts to about 3 parts by weight b), heating the mixture to 90°C or higher for a sufficient time to form a clear liquid mixture of a) and b), adding about 2 parts to about 12 parts by weight c) thereto to obtain a clear liquid blend of a), b) and c) and maintaining the liquid blend at a temperature of from 90°C to 140°C, where the liquid blend of a), b) and c) is stable at the temperature at which it is maintained for greater than 120 hours.
  • the process comprises adding about 5 to about 1 1 parts by weight c) to the liquid mixture of a) and b).
  • the process comprises adding about 8 to about 1 1 parts by weight c) to the liquid mixture of a) and b).
  • the liquid blend of a), b) and c) is maintained at a temperature from 90°C to 125°C.
  • the liquid blend of a), b) and c) is maintained at a temperature from 90°C to 1 10°C.
  • Cooling may be active cooling or allowing slowly to cool at ambient conditions.
  • Stable means no observed precipitation or solids at a certain temperature for greater than a certain length of time.
  • Formulations 3-5 are very stable liquid blends. Higher levels of IRGANOX 1010 are advantageous even though its melting point is much higher than IRGANOX 1076.
  • Example 1 is repeated, except that in this case, glass vials containing mixtures of IRGANOX 1010 and IRGANOX 1076 are placed in an oil bath and heated to greater than 90°C to obtain a clear liquid. IRGAFOS 168 is slowly added to the liquid with stirring to obtain a clear liquid blend. The liquid blends are transferred to ovens set at 150°C, 140°C and 135°C to observe if any precipitation occurs at these temperatures at 24, 48, 72, 96 and 120 hour time periods.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
PCT/US2012/057501 2011-10-10 2012-09-27 Liquid stabilizer mixtures Ceased WO2013055524A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
EP12840357.3A EP2766419B1 (en) 2011-10-10 2012-09-27 Liquid stabilizer mixtures
KR1020147009357A KR102013969B1 (ko) 2011-10-10 2012-09-27 액체 안정화제 혼합물
SG11201401069TA SG11201401069TA (en) 2011-10-10 2012-09-27 Liquid stabilizer mixtures
CN201280049692.8A CN104114628B (zh) 2011-10-10 2012-09-27 液体稳定剂混合物
RU2014118603/04A RU2600321C2 (ru) 2011-10-10 2012-09-27 Жидкие смеси стабилизаторов
IN2605CHN2014 IN2014CN02605A (https=) 2011-10-10 2012-09-27
BR112014008472A BR112014008472A2 (pt) 2011-10-10 2012-09-27 processo para a formação de uma mistura líquida estável
CA2850191A CA2850191C (en) 2011-10-10 2012-09-27 Liquid stabilizer mixtures
JP2014535734A JP6045001B2 (ja) 2011-10-10 2012-09-27 液体安定剤混合物
US14/345,998 US9045618B2 (en) 2011-10-10 2012-09-27 Liquid stabilizer mixtures

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161545323P 2011-10-10 2011-10-10
US61/545,323 2011-10-10

Publications (1)

Publication Number Publication Date
WO2013055524A1 true WO2013055524A1 (en) 2013-04-18

Family

ID=48082293

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2012/057501 Ceased WO2013055524A1 (en) 2011-10-10 2012-09-27 Liquid stabilizer mixtures

Country Status (11)

Country Link
US (1) US9045618B2 (https=)
EP (1) EP2766419B1 (https=)
JP (1) JP6045001B2 (https=)
KR (1) KR102013969B1 (https=)
CN (1) CN104114628B (https=)
BR (1) BR112014008472A2 (https=)
CA (1) CA2850191C (https=)
IN (1) IN2014CN02605A (https=)
RU (1) RU2600321C2 (https=)
SG (1) SG11201401069TA (https=)
WO (1) WO2013055524A1 (https=)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6376551B2 (ja) * 2014-02-20 2018-08-22 日東電工株式会社 光導波路コア形成用液状感光性樹脂組成物およびそれを用いた光導波路、ならびにフレキシブルプリント配線板

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030078340A1 (en) * 2000-02-21 2003-04-24 Fatnes Anne Marie Process for the preparation of additive coated molding powder
US20030146542A1 (en) * 2000-02-21 2003-08-07 Fatnes Anne Marie Process for addition of additives to polymer particles
EP2163577A1 (en) * 2008-09-15 2010-03-17 Armacell Enterprise GmbH Foamed thermoplastic cellular materials obtained by reactive extrusion process and with help of chain-extenders
US20100160509A1 (en) * 2006-10-11 2010-06-24 Mehrdad Yazdani-Pedram Compatibilizers for producing nanocomposites, microcomposites and polymer blends and process for obtaining them
US20100233403A1 (en) * 2003-12-04 2010-09-16 Dow Global Technologies Inc. Stabilized polyethylene material

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1231769B (it) * 1989-08-02 1991-12-21 Himont Inc Procedimento per la stabilizzazione di poliolefine e prodotti da esso ottenuti.
JP3872999B2 (ja) * 2002-04-04 2007-01-24 日本ポリプロ株式会社 塗膜黄変性に優れたポリプロピレン系樹脂組成物及びそれを用いた自動車外装部品
TW200628530A (en) * 2004-12-22 2006-08-16 Clariant Int Ltd Liquid or low melting stabilizr formulations
JP5369985B2 (ja) * 2009-08-07 2013-12-18 東洋紡株式会社 レトルト食品包装用フィルム
JP5680879B2 (ja) * 2010-05-26 2015-03-04 株式会社Adeka 樹脂添加剤マスターバッチ

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030078340A1 (en) * 2000-02-21 2003-04-24 Fatnes Anne Marie Process for the preparation of additive coated molding powder
US20030146542A1 (en) * 2000-02-21 2003-08-07 Fatnes Anne Marie Process for addition of additives to polymer particles
US20100233403A1 (en) * 2003-12-04 2010-09-16 Dow Global Technologies Inc. Stabilized polyethylene material
US20100160509A1 (en) * 2006-10-11 2010-06-24 Mehrdad Yazdani-Pedram Compatibilizers for producing nanocomposites, microcomposites and polymer blends and process for obtaining them
EP2163577A1 (en) * 2008-09-15 2010-03-17 Armacell Enterprise GmbH Foamed thermoplastic cellular materials obtained by reactive extrusion process and with help of chain-extenders

Also Published As

Publication number Publication date
US9045618B2 (en) 2015-06-02
CA2850191A1 (en) 2013-04-18
KR20140077168A (ko) 2014-06-23
CN104114628B (zh) 2016-02-03
EP2766419A1 (en) 2014-08-20
IN2014CN02605A (https=) 2015-08-07
EP2766419A4 (en) 2015-06-10
BR112014008472A2 (pt) 2017-05-16
US20140225038A1 (en) 2014-08-14
JP6045001B2 (ja) 2016-12-14
CA2850191C (en) 2019-09-17
RU2600321C2 (ru) 2016-10-20
KR102013969B1 (ko) 2019-10-21
SG11201401069TA (en) 2014-04-28
JP2014530284A (ja) 2014-11-17
EP2766419B1 (en) 2018-07-18
RU2014118603A (ru) 2015-11-20
CN104114628A (zh) 2014-10-22

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